US5880293A - Method for catalytic conversion of carbon dioxide - Google Patents
Method for catalytic conversion of carbon dioxide Download PDFInfo
- Publication number
- US5880293A US5880293A US08/961,144 US96114497A US5880293A US 5880293 A US5880293 A US 5880293A US 96114497 A US96114497 A US 96114497A US 5880293 A US5880293 A US 5880293A
- Authority
- US
- United States
- Prior art keywords
- process according
- catalyst
- carbon dioxide
- tert
- butyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 34
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 31
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001336 alkenes Chemical class 0.000 claims abstract description 19
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052751 metal Inorganic materials 0.000 claims abstract description 17
- 239000002184 metal Substances 0.000 claims abstract description 17
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 10
- 229940032159 propylene carbonate Drugs 0.000 description 10
- 229910018404 Al2 O3 Inorganic materials 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 229910052692 Dysprosium Inorganic materials 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- -1 indiume Chemical compound 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000379 polypropylene carbonate Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
- C07D317/38—Ethylene carbonate
Definitions
- the invention concerns a process for the conversion of carbon dioxide by a reaction thereof with epoxide (olefin oxide) and a subsequent conversion to alkylenecarbonate.
- epoxide olefin oxide
- alkylenecarbonate epoxide
- tert-butyl-substituted mono- and diphthalocyanine complexes of metals are provided as catalysts for this process.
- the process closest to the present invention is a process for formating alkylenecarbonates using phthalocyanine complexes of metals as catalysts, described in the U.S. Pat. No. 5,283,356.
- a drawback of this method is the low solubility of the used catalysts, that results, apparently, in a heterogeneous progression of the process with very low efficiency.
- a reaction in heterogeneous conditions does not allow to reach quantitative conversion of carbon dioxide, and, accordingly, much reduces the efficiency of said process.
- the present invention provides a process for the catalytic conversion of carbon dioxide by reacting it with an olefin oxide in the presence of a catalyst which is a tert-butyl-substituted phthalocyanine complex of a metal.
- the applicant of the present invention has found that the specified drawback can be eliminated by using an alkyl-substituted phthalocyanine complexe of metal, whose solubility is higher, by several orders of magnitude, than the solubility of a corresponding unsubstututed analogue.
- tert-butyl-substituted phthalocyanine complexes of practically all metals in the periodic table were synthesized. The presence of such substituents on the ring structure in a phthalocyanine molecule results in sharp increases in solubility of complexes (by two times) in organic solvents and, hence, a homogeneous catalytic reaction can proceed.
- the invention concerns a process of assimilating carbon dioxide by a reaction thereof with an olefin oxide followed by a subsequent conversion to alkylenecarbonates.
- catalysts for this process for the first time, tert-butyl-substituted mono- and diphthalocyanine complexes of metals are proposed.
- Propylene oxide, ethylene oxide and epichlorohydrine were chosen as olefin oxides.
- a direct crystallization method was used. The reaction mixtures were subjected to vacuum distillation so as to obtain fractions representing individual compounds confirmed by IR- and NMR 1 H-spectra.
- Ethylenecarbonate has a boiling point of 147°-149° C. (20 Torr)
- propylenecarbonate has a boiling part of 152°-154° C. (20 Torr).
- the reactions proceed at temperature from 100° to 250° C., however the quantitative yield can be achieved at a temperature of 180° C. Although the reaction can be observed at atmospheric pressure, the optimum condition is reached at pressure 50 Atm or above. The required pressure is reached by the introduction of a certain quantity of carbon dioxide. The reaction mixture is heated to certain temperature and maintained for a certain time at the given temperature and the chosen pressure.
- Olefin oxides and carbon dioxide are mixed in a proportion, ensuring an excess of carbon dioxide in comparison with the stoichiometric quantity, required in reaction.
- the excess of carbon dioxide can be from 1.5 mol up to 20 mol for each mol of olefin oxides. It is necessary to avoid an excess of olefin oxide to avoid the formation of undesirable products of the olefin oxides polymerization and the creation of explosive conditions.
- alkylsubstituted mono- and diphthalocyanine complexes of metals are provided as catalysts for carbon dioxide conversion.
- Metalphthalocyanines are represented by the following formulas: ##STR2## Wherein R is an alkyl and M is a 2-, 3- or 4-valent metal, such as aluminum, dysprosium, indiume, chromium etc.
- a quantity of the catalyst used in the present process of carbon dioxide conversion is from 0.05 to 5.0% in relation to the olefin oxide weight.
- An increase in concentration of the catalyst results in a more complete and quick carbon dioxide conversion, all other things being equal.
- the second possibility for enhancing the yield is based on an increase in the number of active centres of catalyst in a reaction mixture (apart from an increase of the catalyst solubility) arranged, by the present inventors, by coating the catalyst on the carrier.
- SiO 2 , neutral Al 2 O 3 and alkaline Al 2 O 3 were tested as carriers. It appeared that the coating of the catalyst on SiO 2 and neutral Al 2 O 3 did not give positive results, while the use of alkaline Al 2 O 3 (Al 2 O 3 /OH - ) improved catalytic activity of the system.
- the catalyst was prepared by dissolving an appropriate substituted phthalocyanine complex of metal in CH 2 Cl 2 , adding a necessary quantity of Al 2 O 3 /OH - and evaporating this mixture in vacuum.
- Unsubstituted phthalocyanine was coated by dissolving it in a large amount of acetone, coating the solution on Al 2 O 3 /OH - and then evaporating the solvent in a vacuum.
- the resulting data provide an effective process for carbon dioxide conversion by the interaction thereof with an olefin oxide followed by a subsequent conversion to alkylenecarbonates.
- tert-butyl-substituted mono- and diphthalocyanine complexes of metals are provided as catalysts for this process.
- the present invention provide a process for carbon dioxide conversion producing alkylenecarbonates which are excellent starting materials for the production of polymers and diols.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Treating Waste Gases (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU96121458 | 1996-10-31 | ||
| RU9696121458A RU2100355C1 (ru) | 1996-10-31 | 1996-10-31 | Способ каталитического связывания двуокиси углерода |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US5880293A true US5880293A (en) | 1999-03-09 |
Family
ID=20187037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US08/961,144 Expired - Lifetime US5880293A (en) | 1996-10-31 | 1997-10-30 | Method for catalytic conversion of carbon dioxide |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5880293A (ru) |
| EP (1) | EP0839811B1 (ru) |
| JP (1) | JP4107697B2 (ru) |
| DE (1) | DE69713245T2 (ru) |
| RU (1) | RU2100355C1 (ru) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040201335A1 (en) * | 2003-03-28 | 2004-10-14 | Brooks Davis | Universal computer enclosure |
| CN101805324A (zh) * | 2010-04-09 | 2010-08-18 | 兰州大学 | 一种环碳酸酯化合物及合成方法 |
| US20110230580A1 (en) * | 2008-09-08 | 2011-09-22 | Novomer, Inc | Polycarbonate polyol compositions and methods |
| US11180609B2 (en) | 2018-08-02 | 2021-11-23 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
| US12195576B2 (en) | 2021-06-23 | 2025-01-14 | Saudi Aramco Technologies Company | Polyol compositions and methods |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2154052C1 (ru) * | 1999-06-03 | 2000-08-10 | Институт физиологически активных веществ РАН | Способ электрокаталитического связывания диоксида углерода с использованием электрополимеризованных фталоцианиновых комплексов |
| AU2001257038A1 (en) | 2000-04-13 | 2001-10-30 | Sun Microsystems, Inc. | Electro-desorption compressor |
| RU2415837C2 (ru) * | 2009-07-14 | 2011-04-10 | ООО "Объединенный центр исследований и разработок" (ООО "ЮРД-Центр") | Способ получения карбамида, меченного стабильным изотопом 13c |
| RU2440826C1 (ru) * | 2010-12-16 | 2012-01-27 | Государственное унитарное предприятие г. Москвы "Международный научный и клинический центр "Интермедбиофизхим" (ГУП "МНКЦ "Интермедбиофизхим") | Способ получения карбамида, меченного стабильным изотопом 13c |
| RU2740944C1 (ru) * | 2019-09-19 | 2021-01-21 | Федеральное государственное бюджетное учреждение науки Институт проблем химической физики Российской академии наук (ИПХФ РАН) | Комплексы металлов с пентадентантными (N3O2) лигандами, способ их получения, каталитические системы для проведения реакций диоксида углерода с эпоксидами, способ получения циклических карбонатов или алифатических поликарбонатов |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2773070A (en) * | 1952-10-31 | 1956-12-04 | Jefferson Chem Co Inc | Catalytic process for producing alkylene carbonates |
| US2873282A (en) * | 1952-04-05 | 1959-02-10 | Jefferson Chem Co Inc | Catalytic process for producing alkylene carbonates |
| US3535341A (en) * | 1968-02-07 | 1970-10-20 | Dow Chemical Co | Process for making alkylene carbonates |
| US4663467A (en) * | 1984-03-05 | 1987-05-05 | The Dow Chemical Company | Novel porphyrinate and amine composition useful as catalysts in the preparation of alkylene carbonates |
| US4786741A (en) * | 1982-11-15 | 1988-11-22 | Scientific Design Company, Inc. | Preparation of alkylene carbonates |
| EP0297647A1 (en) * | 1987-06-19 | 1989-01-04 | Union Carbide Corporation | Process for the production of alkylene carbonate |
| US4892954A (en) * | 1985-08-16 | 1990-01-09 | Hoechst Ag | Process for the preparation of 2-oxo-1,3-dioxolanes |
| US4981948A (en) * | 1988-08-09 | 1991-01-01 | Mitsui Petrochemical Industries, Ltd. | Zinc-containing solid catalyst, process of preparing same and process for preparing polyalkylene carbonate |
| US4982954A (en) * | 1989-03-31 | 1991-01-08 | Janos Lazar | Exercise device of skill and amusement |
| US5283356A (en) * | 1992-08-03 | 1994-02-01 | Texaco Chemical Company | Process for manufacturing alkylene carbonates using metal phthalocyanine catalysts |
| US5631386A (en) * | 1996-08-02 | 1997-05-20 | Arco Chemical Technology, L.P. | Alkylene carbonate recovery |
-
1996
- 1996-10-31 RU RU9696121458A patent/RU2100355C1/ru active
-
1997
- 1997-08-19 JP JP22270397A patent/JP4107697B2/ja not_active Expired - Lifetime
- 1997-10-28 DE DE69713245T patent/DE69713245T2/de not_active Expired - Lifetime
- 1997-10-28 EP EP97118733A patent/EP0839811B1/en not_active Expired - Lifetime
- 1997-10-30 US US08/961,144 patent/US5880293A/en not_active Expired - Lifetime
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2873282A (en) * | 1952-04-05 | 1959-02-10 | Jefferson Chem Co Inc | Catalytic process for producing alkylene carbonates |
| US2773070A (en) * | 1952-10-31 | 1956-12-04 | Jefferson Chem Co Inc | Catalytic process for producing alkylene carbonates |
| US3535341A (en) * | 1968-02-07 | 1970-10-20 | Dow Chemical Co | Process for making alkylene carbonates |
| US4786741A (en) * | 1982-11-15 | 1988-11-22 | Scientific Design Company, Inc. | Preparation of alkylene carbonates |
| US4663467A (en) * | 1984-03-05 | 1987-05-05 | The Dow Chemical Company | Novel porphyrinate and amine composition useful as catalysts in the preparation of alkylene carbonates |
| US4892954A (en) * | 1985-08-16 | 1990-01-09 | Hoechst Ag | Process for the preparation of 2-oxo-1,3-dioxolanes |
| EP0297647A1 (en) * | 1987-06-19 | 1989-01-04 | Union Carbide Corporation | Process for the production of alkylene carbonate |
| US4981948A (en) * | 1988-08-09 | 1991-01-01 | Mitsui Petrochemical Industries, Ltd. | Zinc-containing solid catalyst, process of preparing same and process for preparing polyalkylene carbonate |
| US4982954A (en) * | 1989-03-31 | 1991-01-08 | Janos Lazar | Exercise device of skill and amusement |
| US5283356A (en) * | 1992-08-03 | 1994-02-01 | Texaco Chemical Company | Process for manufacturing alkylene carbonates using metal phthalocyanine catalysts |
| US5631386A (en) * | 1996-08-02 | 1997-05-20 | Arco Chemical Technology, L.P. | Alkylene carbonate recovery |
Non-Patent Citations (7)
| Title |
|---|
| Chemical Abstracts No. XP002055596, vol. 124, No. 9, 1996; K. Kasuga et al; Cycloaddition of Carbon Dioxide . . ., p. 1183. * |
| Kasuga et al. Cycloaddition of Carbon Dioxide to Propylene Oxide catalysed by Tetra t butylphthalocyaninatoaluminium (III) Chloride, Polyhedron, vol. 15, No. 1, pp. 69 72, 1996, Nov. 1995. * |
| Kasuga et al. Cycloaddition of Carbon Dioxide to Propylene Oxide catalysed by Tetra-t-butylphthalocyaninatoaluminium (III) Chloride, Polyhedron, vol. 15, No. 1, pp. 69-72, 1996, Nov. 1995. |
| Kuninobu Kasuga et al., Cycloaddition of Carbon Dioxide . . ., vol. 69, No. 10, Oct. 1996 pp. 2885 2888; XP002055595. * |
| Kuninobu Kasuga et al., Cycloaddition of Carbon Dioxide . . ., vol. 69, No. 10, Oct. 1996 pp. 2885-2888; XP002055595. |
| Polyhedron, vol. 15, No. 1, 1996, JP, pp. 69 72. * |
| Polyhedron, vol. 15, No. 1, 1996, JP, pp. 69-72. |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040201335A1 (en) * | 2003-03-28 | 2004-10-14 | Brooks Davis | Universal computer enclosure |
| US8604155B2 (en) | 2008-09-08 | 2013-12-10 | Novomer, Inc. | Polycarbonate polyol compositions and methods |
| US9376531B2 (en) | 2008-09-08 | 2016-06-28 | Novomer, Inc. | Polycarbonate polyol compositions and methods |
| US8247520B2 (en) | 2008-09-08 | 2012-08-21 | Novomer, Inc. | Polycarbonate polyol compositions and methods |
| US11535706B2 (en) | 2008-09-08 | 2022-12-27 | Saudi Aramco Technologies Company | Polycarbonate polyol compositions and methods |
| US8470956B2 (en) | 2008-09-08 | 2013-06-25 | Novomer, Inc. | Polycarbonate polyol compositions and methods |
| US10836859B2 (en) | 2008-09-08 | 2020-11-17 | Saudi Aramco Technologies Company | Polycarbonate polyol compositions and methods |
| US8921508B2 (en) | 2008-09-08 | 2014-12-30 | Novomer, Inc. | Polycarbonate polyol compositions and methods |
| US20110230580A1 (en) * | 2008-09-08 | 2011-09-22 | Novomer, Inc | Polycarbonate polyol compositions and methods |
| US9809678B2 (en) | 2008-09-08 | 2017-11-07 | Saudi Aramco Technologies Company | Polycarbonate polyol compositions and methods |
| US10301426B2 (en) | 2008-09-08 | 2019-05-28 | Saudi Aramco Technologies Company | Polycarbonate polyol compositions and methods |
| CN101805324A (zh) * | 2010-04-09 | 2010-08-18 | 兰州大学 | 一种环碳酸酯化合物及合成方法 |
| CN101805324B (zh) * | 2010-04-09 | 2013-01-23 | 兰州大学 | 一种环碳酸酯化合物及合成方法 |
| US11180609B2 (en) | 2018-08-02 | 2021-11-23 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
| US12195576B2 (en) | 2021-06-23 | 2025-01-14 | Saudi Aramco Technologies Company | Polyol compositions and methods |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69713245D1 (de) | 2002-07-18 |
| EP0839811A1 (en) | 1998-05-06 |
| JP4107697B2 (ja) | 2008-06-25 |
| EP0839811B1 (en) | 2002-06-12 |
| RU2100355C1 (ru) | 1997-12-27 |
| JPH10165762A (ja) | 1998-06-23 |
| DE69713245T2 (de) | 2003-01-23 |
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